Guaiazulene

Title: Guaiazulene
CAS Registry Number: 489-84-9
CAS Name: 1,4-Dimethyl-7-(1-methylethyl)azulene
Additional Names: 7-isopropyl-1,4-dimethylazulene; S-guaiazulene
Trademarks: AZ 8 (Millet Roux); AZ 8 Beris (Weimer); Eucazulen; Kessazulen; Vaumigan
Molecular Formula: C15H18
Molecular Weight: 198.30
Percent Composition: C 90.85%, H 9.15%
Literature References: Isoln from chamomile oil: Sorm et al., Collect. Czech. Chem. Commun. 16, 626 (1951); from guaiac wood oil: Joos, CH 314487 (1956), C.A. 52, 443b (1958). Total synthesis: Plattner et al., Helv. Chim. Acta 32, 2452 (1949); Sorm et al., Collect. Czech. Chem. Commun. 16, 168 (1951); Jacob et al., Tetrahedron 20, 2821 (1964); J. Mukherjee et al., J. Am. Chem. Soc. 101, 251 (1979). Pharmacokinetics of guaiazulene soluble in animals: H. Mukai et al., J. Pharmacobio-Dyn. 8, 329, 337 (1985). Effect on gastric and duodenal ulcers in rats: S. Okabe et al., Nippon Yakurigaku Zasshi 88, 467 (1986), C.A. 106, 43769 (1987).
Properties: Blue oil. bp10 165-170°.
Boiling point: bp10 165-170°
Derivative Type: 3-Sulfonate sodium salt
CAS Registry Number: 6223-35-4
Additional Names: 5-Isopropyl-3,8-dimethyl-1-azulenesulfonic acid sodium salt; sodium gualenate; guaiazulene soluble
Trademarks: Azulon (Rorer)
Molecular Formula: C15H17NaO3S
Molecular Weight: 300.35
Percent Composition: C 59.98%, H 5.71%, Na 7.65%, O 15.98%, S 10.68%
Derivative Type: Trinitrobenzene deriv
CAS Registry Number: 4968-29-0
Molecular Formula: C15H18.C6H3N3O6
Molecular Weight: 411.41
Percent Composition: C 61.31%, H 5.14%, N 10.21%, O 23.33%
Properties: Violet to black needles from ethanol, mp 151°.
Melting point: mp 151°
Therap-Cat: Anti-inflammatory; antiulcerative.
Keywords: Anti-inflammatory (Nonsteroidal); Antiulcerative; Cytoprotectant (Gastric).
Guaiol Guamecycline Guanabenz Guanacline Guanadrel

Guaiazulene
Guaiazulene
Identifiers
CAS number 489-84-9 YesY
PubChem 3515
ChemSpider 3395 YesY
UNII 2OZ1K9JKQC YesY
KEGG D01037 YesY
ChEBI CHEBI:5550 YesY
ATC code S01XA01
Jmol-3D images Image 1
Properties
Molecular formula C15H18
Molar mass 198.31 g/mol
Density 0.976 g/cm3
Melting point 31-33 °C
Boiling point 153 °C (7 mm Hg)
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Guaiazulene, also azulon or 1,4-dimethyl-7-isopropylazulene, is a dark blue crystalline hydrocarbon. A derivative of azulene, guaiazulene is a bicyclic sesquiterpene that is a constituent of some essential oils, mainly oil of guaiac and chamomile oil, which also serve as its commercial sources. Various soft corals also contain guaiazulene as a principal pigment.[1] Its low melting point makes guaiazulene difficult to handle, in contrast to the crystalline nature of the parent azulene. The electronic structure (and colors) of guaiazulene and azulene are very similar.

The blue color of the mushroom Lactarius indigo is due to the guaiazulene derivative (7-isopropenyl-4-methylazulen-1-yl)methyl stearate.[2]